Do I want my final project to be printed or digital? How is going to be used/held? What other constraints do I need to keep in mind moving forward?

I'm planning for a static digital map or map series, viewed primarily on the desktop. The challenge will be to present the different routes over time and the obstacles which shaped them in an uncluttered way.

What level of detail do I need to include?

The total area concerned is about 4 square miles; street names and landmarks will be the key details